Sodium Iodide → Methyl 5-chloro-3-formyl-2-(2-methoxy-2-oxoethoxy)benzoate

Participants

Reaction Steps

A solution of methyl 5-chloro-3-formyl-2-hydroxybenzoate (6.4 g, 30 mmol) in acetone (50 mL) was added with potassium carbonate (7.4 g, 54 mmol), the mixture was successively added with sodium iodide (0.60 g, 3.0 mmol) and methyl bromoacetate (6.9 g, 45 mmol), and the mixture was stirred at room temperature for 10 hours, and then refluxed for 5 hours by heating. The reaction mixture was cooled to room temperature, and then added with acetone, and the mixture was filtered through Celite. The solvent was evaporated from the filtrate under reduced pressure, the solid formed was suspended in hexane/ethyl acetate (9:1), thereby washed, and then collected by filtration to obtain the objective substance. The filtrate was concentrated under reduced pressure, and the residue was subjected to by silica gel column chromatography (eluted with hexane/ethyl acetate (9:1→1:1)) to further obtain the objective substance. Two portions of the objective substance were combined to obtain 6.5 g (75%) of methyl 5-chloro-3-formyl-2-(2-methoxy-2-oxoethoxy)benzoate.

Provenance & Evidence